Reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:9]=[C:8]2[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)=[N+]=[N-]>C(O)C.O1CCCC1.C(=O)([O-])[O-].[Ca+2].[Pd+2].C(=O)([O-])[O-]>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:9]=[C:8]2[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 550 mg of tert-butyl 5-(azidomethyl)-3-(3-fluorophenyl)-1H-1-indazolecarboxylate in a mixture of 10 ml ethanol and 5 ml tetrahydrofuran was added 110 mg of 5% palladium-calcium carbonate, and the mixture was hydrogenated at room temperature at normal pressure for 1.5 hours. After filtering off the catalyst through Celite, the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:methanol=1:0 to 9:1), to give 427 mg of the title compound as light green crystals.
Workup
- filtrationAfter filtering off the catalyst through Celite
- customthe solvent was evaporated
- customThe crude product was purified
- customseparated by silica gel column chromatography (ethyl acetate:methanol=1:0 to 9:1)
Sources & evidence
- ORD record
- ord-01b3eb8d0db04ee791c2ab1a5403c76a
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982274B2
Linked notes
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